NP-MRD: Showing NP-Card for (3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate (NP0220404)

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Record Information

Version

2.0

Created at

2022-09-05 21:42:24 UTC

Updated at

2022-09-05 21:42:24 UTC

NP-MRD ID

NP0220404

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate

Description

Pinnatifinoside B belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). (3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate is found in Crataegus pinnatifida. (3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate was first documented in 2001 (PMID: 11454353). Based on a literature review very few articles have been published on Pinnatifinoside B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052223422D          

 33 37  0  0  1  0            999 V2000
    7.7805    0.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1871    0.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3866   -0.4632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3940    0.5647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8006   -0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0075    0.2190    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3574   -0.2889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6735    0.1725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9895    0.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3394    0.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6215   -0.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912   -1.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2788   -1.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484   -1.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966   -0.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -0.8514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    1.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1502    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6623    2.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9444    2.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4141    3.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6963    4.2888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3983    3.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6805    2.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269    0.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4460   -0.6205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009    0.9655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3930    1.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7254    0.9943    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1867    1.6782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 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
 20 26  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 10 28  2  0  0  0  0
 15 28  1  0  0  0  0
 11 29  1  0  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -7.2360    2.7243   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8460    2.1573   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0083    2.4474    0.7081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5705    1.3690   -1.2392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4170    0.7395   -1.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9565   -0.4435   -0.8279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7281   -0.8603   -1.3989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7884   -0.9455   -0.4134 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3853   -0.7123   -0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948   -1.4891    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4538   -2.3907    0.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0060   -3.2326    1.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3425   -3.2003    2.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -4.0503    3.1250 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1754   -2.2861    1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5072   -2.1643    1.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192   -2.8799    2.7616 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2834   -1.2135    1.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7475   -0.4134    0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5501    0.5872   -0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9440    1.3747   -1.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6662    2.3252   -2.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9961    2.5360   -1.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7359    3.4826   -2.5227 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6154    1.7729   -0.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8811    0.8118   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4814   -0.5463   -0.0478 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7122   -1.4374    0.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7343   -2.2526    0.1704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2682    0.0138    0.6517 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1829    1.3253    0.2729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7469   -0.4343    0.6267 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6512   -1.8048    1.0174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2834    3.4467    0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9517    1.8861    0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4764    3.2198   -0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5197    0.3926   -2.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5851    1.5171   -1.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6766   -1.2848   -1.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0216    0.3099   -0.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2313   -1.2281   -1.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6618   -3.9600    2.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5705   -4.2449    3.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3175   -1.1396    1.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8808    1.2248   -1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1323    2.9040   -2.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8305    4.4456   -2.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6611    1.8967   -0.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3982    0.2317    0.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8225   -0.2006    1.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5460    1.5496   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3891    0.1012    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4596   -1.9776    1.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  6
  8  9  1  0
  9 10  1  0
 10 28  2  0
 28 27  1  0
 27 19  1  0
 19 18  2  0
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 11  2  0
 11 29  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
  8 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32  6  1  0
 29  8  1  0
 26 20  1  0
 11 10  1  0
 15 28  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  1
  9 40  1  0
  9 41  1  0
 18 44  1  0
 14 43  1  0
 12 42  1  0
 21 45  1  0
 22 46  1  0
 24 47  1  0
 25 48  1  0
 26 49  1  0
 30 50  1  1
 31 51  1  0
 32 52  1  1
 33 53  1  0
M  END


  Mrv1652309052223422D          

 33 37  0  0  1  0            999 V2000
    7.7805    0.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1871    0.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3866   -0.4632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3940    0.5647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8006   -0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0075    0.2190    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3574   -0.2889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6735    0.1725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9895    0.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3394    0.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6215   -0.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912   -1.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2788   -1.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7484   -1.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966   -0.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462   -0.8514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    1.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1502    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6623    2.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9444    2.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4141    3.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6963    4.2888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3983    3.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6805    2.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269    0.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4460   -0.6205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9009    0.9655    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3930    1.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7254    0.9943    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1867    1.6782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 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
 20 26  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 10 28  2  0  0  0  0
 15 28  1  0  0  0  0
 11 29  1  0  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0220404

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@@]2(CC3=C4OC(=CC(=O)C4=C(O)C=C3O2)C2=CC=C(O)C=C2)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O10/c1-10(24)30-9-18-20(28)22(29)23(33-18)8-13-17(32-23)7-15(27)19-14(26)6-16(31-21(13)19)11-2-4-12(25)5-3-11/h2-7,18,20,22,25,27-29H,8-9H2,1H3/t18-,20-,22+,23+/m1/s1

> <INCHI_KEY>
JPQIZNMBTLLOPM-SQMBMXPBSA-N

> <FORMULA>
C23H20O10

> <MOLECULAR_WEIGHT>
456.403

> <EXACT_MASS>
456.105646844

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
45.362939972720916

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(3'S,4'S,5'R,8R)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-4,9-dihydrospiro[furo[2,3-h]chromene-8,2'-oxolane]-5'-yl]methyl acetate

> <JCHEM_LOGP>
1.5555754029999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.751679932797408

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.508259138015699

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6851353463651186

> <JCHEM_POLAR_SURFACE_AREA>
151.98000000000002

> <JCHEM_REFRACTIVITY>
111.77490000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3'S,4'S,5'R,8R)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9H-spiro[furo[2,3-h]chromene-8,2'-oxolane]-5'-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      14.524   1.699   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.416   0.630   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.788  -0.865   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.936   1.054   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.828  -0.016   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.347   0.409   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.134  -0.539   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.857   0.322   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.580   1.183   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.367   0.235   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.894  -1.212   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.904  -2.392   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.387  -2.124   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.397  -3.304   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.860  -0.677   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.344  -0.410   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.646  -1.589   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.183   1.037   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.807   2.217   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.280   3.664   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.236   3.932   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.763   5.379   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.773   6.559   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.300   8.006   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.744   6.291   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.270   4.844   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.324   1.950   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.850   0.503   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.433  -1.158   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.282   1.802   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.334   3.016   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.821   1.856   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.682   3.133   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   29   30                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   28                                                  
CONECT   11   10   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   28                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20                                                       
CONECT   27   19   28                                                       
CONECT   28   27   10   15                                                  
CONECT   29   11    8                                                       
CONECT   30    8   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    6   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₀O₁₀

Average Mass

456.4030 Da

Monoisotopic Mass

456.10565 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@@]2(CC3=C4OC(=CC(=O)C4=C(O)C=C3O2)C2=CC=C(O)C=C2)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C23H20O10/c1-10(24)30-9-18-20(28)22(29)23(33-18)8-13-17(32-23)7-15(27)19-14(26)6-16(31-21(13)19)11-2-4-12(25)5-3-11/h2-7,18,20,22,25,27-29H,8-9H2,1H3/t18-,20-,22+,23+/m1/s1

InChI Key

JPQIZNMBTLLOPM-SQMBMXPBSA-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
Crataegus pinnatifida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Ketal
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Pyran
Heteroaromatic compound
Vinylogous acid
Tetrahydrofuran
Carboxylic acid ester
1,2-diol
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Polyol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00037649

Chemspider ID

552608

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636920

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang PC, Xu SX: Flavonoid ketohexosefuranosides from the leaves of Crataegus pinnatifida Bge. var. major N.E.Br. Phytochemistry. 2001 Aug;57(8):1249-53. doi: 10.1016/s0031-9422(01)00170-4. [PubMed:11454353 ]
LOTUS database [Link]

Showing NP-Card for (3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate (NP0220404)

MOL for NP0220404 ((3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate)

3D MOL for NP0220404 ((3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate)

3D SDF for NP0220404 ((3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate)

3D-SDF for NP0220404 ((3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate)

PDB for NP0220404 ((3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate)

3D PDB for NP0220404 ((3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate)

SMILES for NP0220404 ((3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate)

INCHI for NP0220404 ((3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate)

Structure for NP0220404 ((3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate)

3D Structure for NP0220404 ((3's,4's,5'r,8r)-3',4',5-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-9h-spiro[furo[2,3-h]chromene-8,2'-oxolan]-5'-ylmethyl acetate)