NP-MRD: Showing NP-Card for 4-O-Galloylbergenin (NP0138259)

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Record Information

Version

2.0

Created at

2022-05-31 17:17:33 UTC

Updated at

2022-05-31 17:17:33 UTC

NP-MRD ID

NP0138259

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-O-Galloylbergenin

Description

4-O-Galloylbergenin belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. 4-O-Galloylbergenin is found in Lotus corniculatus and Rodgersia podophylla. 4-O-Galloylbergenin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241504112D          

 34 37  0  0  0  0            999 V2000
    1.2079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829    3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954    2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2204    2.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 16 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  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
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  1  0  0  0  0
  7 32  1  0  0  0  0
 32 33  2  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -6.2156   -0.0638    2.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2014   -0.1303    1.0296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0646   -0.7858    0.4995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0790   -2.1411    0.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2111   -2.8663    0.5792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9658   -2.7609   -0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8091   -2.0365   -0.5439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7786   -0.6885   -0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9277   -0.0777    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9332    1.2763    0.4214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5871    0.1523   -0.6357 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8803    0.8482   -1.7916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8026    1.2707   -2.5212 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0583    2.5481   -3.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333    2.8543   -3.9838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4580    1.4385   -1.7086 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3099    2.3460   -0.6746 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428    0.0576   -1.2130 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8544    0.2363   -0.2451 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1550   -0.2072   -0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4386   -0.8068   -1.4550 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1795   -0.0094    0.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4510   -0.4864    0.3987 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4795   -0.3424    1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7659   -0.8356    1.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2435    0.3112    2.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3029    0.4368    3.3945 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9737    0.7968    2.7551 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7106    1.4495    3.9418 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9531    0.6327    1.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3520   -0.6653   -0.6844 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5284   -1.9032   -1.3648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   -2.7038   -1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6590   -3.9434   -1.2867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0079    0.6179    2.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1943    0.2492    2.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3905   -1.1279    2.7913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2821   -3.8659    0.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9132   -3.8253   -0.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1774    1.9072    0.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850    0.8420    0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5782    0.4816   -3.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2275    3.4106   -2.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8493    2.4306   -4.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4562    2.0627   -4.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2415    1.8474   -2.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4339    2.9711   -0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2254   -0.4899   -2.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6965   -1.0095   -0.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9296   -1.3104    0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2115    0.8947    4.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3577    1.6168    4.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9651    1.0257    2.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1065   -0.9566    0.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7 33  1  0
 33 34  2  0
 33 32  1  0
 32 31  1  0
 31 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  2  0
 18 16  1  0
 16 17  1  0
 16 13  1  0
 13 14  1  0
 14 15  1  0
 13 12  1  0
 12 11  1  0
 11  8  1  0
  8  9  2  0
  9 10  1  0
  9  3  1  0
  8  7  1  0
 11 31  1  0
 30 22  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  5 38  1  0
  6 39  1  0
 31 54  1  1
 18 48  1  6
 23 49  1  0
 25 50  1  0
 27 51  1  0
 29 52  1  0
 30 53  1  0
 16 46  1  6
 17 47  1  0
 13 42  1  6
 14 43  1  0
 14 44  1  0
 15 45  1  0
 11 41  1  1
 10 40  1  0
M  END


  Mrv1533004241504112D          

 34 37  0  0  0  0            999 V2000
    1.2079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579    3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829    3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954    2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2204    2.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 16 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  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
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 11 31  1  0  0  0  0
 31 32  1  0  0  0  0
  7 32  1  0  0  0  0
 32 33  2  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138259

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(=O)OC3C(OC(=O)C4=CC(O)=C(O)C(O)=C4)C(O)C(CO)OC3C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O13/c1-31-16-10(25)4-7-12(15(16)28)17-19(34-21(7)30)18(14(27)11(5-22)32-17)33-20(29)6-2-8(23)13(26)9(24)3-6/h2-4,11,14,17-19,22-28H,5H2,1H3

> <INCHI_KEY>
QKSHSFQTWCKTFV-UHFFFAOYSA-N

> <FORMULA>
C21H20O13

> <MOLECULAR_WEIGHT>
480.378

> <EXACT_MASS>
480.090390704

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.757140561020506

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,12,14-trihydroxy-4-(hydroxymethyl)-13-methoxy-9-oxo-3,8-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(14),10,12-trien-6-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
0.35778091833333353

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.731973572728766

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.988438588149138

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9792118771788214

> <JCHEM_POLAR_SURFACE_AREA>
212.66999999999996

> <JCHEM_REFRACTIVITY>
109.13

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,12,14-trihydroxy-4-(hydroxymethyl)-13-methoxy-9-oxo-3,8-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(14),10,12-trien-6-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.255  -4.207   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.795  -4.207   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.255  -1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.105   2.461   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       8.415   1.127   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.495   1.127   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.725   2.461   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.185   2.461   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.495   3.795   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.725   5.128   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.495   6.462   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.725   7.796   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.035   6.462   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.805   7.796   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.805   5.128   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      15.345   5.128   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.035   3.795   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.035  -1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.495  -4.207   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.725  -5.541   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.185  -2.874   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.875  -4.207   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   32                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   31                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   16                                                       
CONECT   25   12   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31                                                       
CONECT   31   30   11   32                                                  
CONECT   32   31    7   33                                                  
CONECT   33   32    3   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
5,12,14-Trihydroxy-4-(hydroxymethyl)-13-methoxy-9-oxo-3,8-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(14),10,12-trien-6-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₁H₂₀O₁₃

Average Mass

480.3780 Da

Monoisotopic Mass

480.09039 Da

IUPAC Name

5,12,14-trihydroxy-4-(hydroxymethyl)-13-methoxy-9-oxo-3,8-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(14),10,12-trien-6-yl 3,4,5-trihydroxybenzoate

Traditional Name

5,12,14-trihydroxy-4-(hydroxymethyl)-13-methoxy-9-oxo-3,8-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(14),10,12-trien-6-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

82958-45-0

SMILES

COC1=C(O)C=C2C(=O)OC3C(OC(=O)C4=CC(O)=C(O)C(O)=C4)C(O)C(CO)OC3C2=C1O

InChI Identifier

InChI=1S/C21H20O13/c1-31-16-10(25)4-7-12(15(16)28)17-19(34-21(7)30)18(14(27)11(5-22)32-17)33-20(29)6-2-8(23)13(26)9(24)3-6/h2-4,11,14,17-19,22-28H,5H2,1H3

InChI Key

QKSHSFQTWCKTFV-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
Lotus corniculatus	LOTUS Database	35616633
Rodgersia podophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
Hydroxysteroid
3-hydroxysteroid
16-oxosteroid
1-hydroxysteroid
Oxosteroid
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Isochromane
Benzopyran
2-benzopyran
Benzoate ester
Pyrogallol derivative
Benzenetriol
Benzoic acid or derivatives
Benzoyl
Anisole
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Oxane
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Lactone
Dialkyl ether
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Primary alcohol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

16-oxo steroid (CHEBI:81148 )

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	1.06	ALOGPS
logP	0.36	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	7.99	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	212.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.13 m³·mol⁻¹	ChemAxon
Polarizability	44.76 Å³	ChemAxon
Number of Rings	4	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

C00029277

Chemspider ID

Not Available

KEGG Compound ID

C17514

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14464332

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-O-Galloylbergenin (NP0138259)

MOL for NP0138259 (4-O-Galloylbergenin)

3D MOL for NP0138259 (4-O-Galloylbergenin)

3D SDF for NP0138259 (4-O-Galloylbergenin)

3D-SDF for NP0138259 (4-O-Galloylbergenin)

PDB for NP0138259 (4-O-Galloylbergenin)

3D PDB for NP0138259 (4-O-Galloylbergenin)

SMILES for NP0138259 (4-O-Galloylbergenin)

INCHI for NP0138259 (4-O-Galloylbergenin)

Structure for NP0138259 (4-O-Galloylbergenin)

3D Structure for NP0138259 (4-O-Galloylbergenin)