NP-MRD: Showing NP-Card for 3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid (NP0278302)

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Record Information

Version

2.0

Created at

2022-09-09 03:16:31 UTC

Updated at

2022-09-09 03:16:31 UTC

NP-MRD ID

NP0278302

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid

Description

Sanguisorbic acid dilactone belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. 3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid is found in Rosa henryi. 3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid was first documented in 2020 (PMID: 33274939). Based on a literature review a small amount of articles have been published on Sanguisorbic acid dilactone (PMID: 35906097) (PMID: 35309515) (PMID: 33965762) (PMID: 32648752).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092205162D          

 34 38  0  0  0  0            999 V2000
    8.0289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7914   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2039    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7914    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2039    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664   -0.1105    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 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  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 32  2  0  0  0  0
 32 33  1  0  0  0  0
 21 33  1  0  0  0  0
 27 33  2  0  0  0  0
 10 34  2  0  0  0  0
  4 34  1  0  0  0  0
M  END

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
   -5.4293    3.3598    1.6588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7903    2.2665    1.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1438    2.0045    1.0791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8255    1.2414    0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2624    0.0437    0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3461   -0.8943   -0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7563   -2.1317   -0.6663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9661   -0.6487   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1039   -1.6615   -0.4656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493    0.5480    0.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2568    0.9085    0.6342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1463    0.9978   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0288    1.9031   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9859    2.7701   -1.4266 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2389    1.9166   -1.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3975    2.7303   -2.7221 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2711    1.0424   -1.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091    1.0367   -2.1138 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3936    0.2007   -1.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6032    0.2079   -2.4902 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2595   -0.7150   -0.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2608   -1.5928   -0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0697   -2.4951    0.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1427   -3.3345    0.9025 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8847   -2.5234    1.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7594   -3.3484    2.2585 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956   -1.6440    0.9591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7527   -1.6295    1.5865 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7886   -0.7987    1.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3754   -0.8539    1.9707 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058    0.1136    0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0846    0.1429   -0.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0814   -0.7557   -0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5024    1.5036    0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7264    2.7712    0.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3294   -0.1597    0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0767   -2.7987   -0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1436   -1.7085   -0.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8606    2.8302   -0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7448   -0.5485   -3.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1848   -1.5571   -0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0718   -4.0100    1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743   -0.2405    2.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1784    2.4653    1.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 32  2  0
 32 31  1  0
 31 29  2  0
 29 30  1  0
 29 28  1  0
 28 27  1  0
 27 33  2  0
 33 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 21 19  2  0
 19 20  1  0
 19 18  1  0
 10 34  2  0
 34  4  1  0
 31 12  1  0
 25 27  1  0
 18 17  1  0
 33 32  1  0
  3 35  1  0
  5 36  1  0
  7 37  1  0
  9 38  1  0
 14 39  1  0
 30 43  1  0
 22 41  1  0
 24 42  1  0
 20 40  1  0
 34 44  1  0
M  END


  Mrv1652309092205162D          

 34 38  0  0  0  0            999 V2000
    8.0289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7914   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2039    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7914    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2039    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664   -0.1105    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 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  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 32  2  0  0  0  0
 32 33  1  0  0  0  0
 21 33  1  0  0  0  0
 27 33  2  0  0  0  0
 10 34  2  0  0  0  0
  4 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0278302

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC(O)=C(O)C(OC2=C(O)C(=O)C3=C4C2=C(O)OC2=C4C(C=C(O)C2=O)=C(O)O3)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H10O13/c22-6-1-4(19(28)29)2-8(12(6)24)32-18-11-10-9-5(20(30)33-17(10)14(26)15(18)27)3-7(23)13(25)16(9)34-21(11)31/h1-3,22-24,27,30-31H,(H,28,29)

> <INCHI_KEY>
KENINNFPWDPMKJ-UHFFFAOYSA-N

> <FORMULA>
C21H10O13

> <MOLECULAR_WEIGHT>
470.298

> <EXACT_MASS>
470.012140382

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
40.70722805143318

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid

> <JCHEM_LOGP>
0.1197049024890895

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
5.481366723463367

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9813092380782744

> <JCHEM_PKA_STRONGEST_BASIC>
3.08488820558811

> <JCHEM_POLAR_SURFACE_AREA>
220.50999999999996

> <JCHEM_REFRACTIVITY>
131.81199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  O   UNK     0      14.987  -1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      13.447  -1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.677  -2.874   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      12.677  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.447   1.127   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.677   2.461   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.447   3.795   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.137   2.461   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.367   3.795   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.367   1.127   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.827   1.127   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.057  -0.206   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.827  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.367  -1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.057  -2.874   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.827  -4.207   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.517  -2.874   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.747  -4.207   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.207  -4.207   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.437  -5.541   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.437  -2.874   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.897  -2.874   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.413  -1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.127   1.127   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.437  -0.206   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.207   1.127   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.747   1.127   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.517   2.461   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.517  -0.206   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.137  -0.206   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   34                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   32                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   33                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   12   32                                                  
CONECT   32   31   17   33                                                  
CONECT   33   32   21   27                                                  
CONECT   34   10    4                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
Sanguisorbate dilactone	Generator

Chemical Formula

C₂₁H₁₀O₁₃

Average Mass

470.2980 Da

Monoisotopic Mass

470.01214 Da

IUPAC Name

3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid

Traditional Name

3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(O)=C(O)C(OC2=C(O)C(=O)C3=C4C2=C(O)OC2=C4C(C=C(O)C2=O)=C(O)O3)=C1

InChI Identifier

InChI=1S/C21H10O13/c22-6-1-4(19(28)29)2-8(12(6)24)32-18-11-10-9-5(20(30)33-17(10)14(26)15(18)27)3-7(23)13(25)16(9)34-21(11)31/h1-3,22-24,27,30-31H,(H,28,29)

InChI Key

KENINNFPWDPMKJ-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
Rosa henryi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acid and derivatives

Alternative Parents

Substituents

Gallic acid or derivatives
Diaryl ether
Coumarin
2-benzopyran
1-benzopyran
Benzopyran
Benzoic acid
Phenoxy compound
Phenol ether
Catechol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Heteroaromatic compound
Vinylogous ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.12	ChemAxon
pKa (Strongest Acidic)	3.98	ChemAxon
pKa (Strongest Basic)	3.08	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	220.51 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	131.81 m³·mol⁻¹	ChemAxon
Polarizability	40.71 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

136784551

PDB ID

Not Available

ChEBI ID

169061

Good Scents ID

Not Available

References

General References

Su L, Zeng Y, Li G, Chen J, Chen X: Quercetin improves high-fat diet-induced obesity by modulating gut microbiota and metabolites in C57BL/6J mice. Phytother Res. 2022 Dec;36(12):4558-4572. doi: 10.1002/ptr.7575. Epub 2022 Jul 29. [PubMed:35906097 ]
Gu W, Wang H, Su M, Wang Y, Xu F, Hu Q, Cai X, Song J, Tong H, Qian Y, Zhao H, Chen J: Investigation of Tannins Transformation in Sanguisorbae Radix Over Carbonizing by Stir-Frying. Front Mol Biosci. 2022 Mar 2;9:762224. doi: 10.3389/fmolb.2022.762224. eCollection 2022. [PubMed:35309515 ]
Tarone AG, Goupy P, Ginies C, Marostica MR Junior, Dufour C: Advanced characterization of polyphenols from Myrciaria jaboticaba peel and lipid protection in in vitro gastrointestinal digestion. Food Chem. 2021 Oct 15;359:129959. doi: 10.1016/j.foodchem.2021.129959. Epub 2021 Apr 27. [PubMed:33965762 ]
Reis SF, Teixeira T, Pinto J, Oliveira V, Lopes P, Cabral M, Mateus N, Guedes de Pinho P, Pereira H, de Freitas V: Variation in the Phenolic Composition of Cork Stoppers from Different Geographical Origins. J Agric Food Chem. 2020 Dec 16;68(50):14970-14977. doi: 10.1021/acs.jafc.0c00586. Epub 2020 Dec 4. [PubMed:33274939 ]
Macierzynski J, Sojka M, Kosmala M, Karlinska E: Transformation of Oligomeric Ellagitannins, Typical for Rubus and Fragaria Genus, during Strong Acid Hydrolysis. J Agric Food Chem. 2020 Aug 5;68(31):8212-8222. doi: 10.1021/acs.jafc.0c02674. Epub 2020 Jul 21. [PubMed:32648752 ]
LOTUS database [Link]

Showing NP-Card for 3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid (NP0278302)

MOL for NP0278302 (3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid)

3D MOL for NP0278302 (3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid)

3D SDF for NP0278302 (3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid)

3D-SDF for NP0278302 (3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid)

PDB for NP0278302 (3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid)

3D PDB for NP0278302 (3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid)

SMILES for NP0278302 (3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid)

INCHI for NP0278302 (3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid)

Structure for NP0278302 (3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid)

3D Structure for NP0278302 (3,4-dihydroxy-5-({3,6,10,13-tetrahydroxy-7,14-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),3,5,8(16),10,12-hexaen-5-yl}oxy)benzoic acid)